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| Terra Wortmann Open | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Aslan Karatsev | Win | 6-7 (4-7), 6-1, 6-2 |
| Second Round | Laslo Djere | Win | 7-6 (7-4), 6-4 |
| Quarterfinals | Oscar Otte | Loss | 6-4, 6-7 (5-7), 4-6 |
| Libema Open | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Alejandro Tabilo | Win | 6-3, 6-3 |
| Second Round | Kamil Majchrzak | Win | 5-7, 7-5, 7-6 (7-5) |
| Quarterfinals | Felix Auger-Aliassime | Loss | 6-7 (5-7), 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Nuno Borges | Win | 6-3, 2-6, 6-4, 6-4 |
| Second Round | Hugo Dellien | Win | 4-6, 6-4, 7-6 (7-1), 6-3 |
| Third Round | Cameron Norrie | Win | 6-2, 7-5, 5-7, 6-4 |
| Fourth Round | Carlos Alcaraz | Loss | 1-6, 4-6, 4-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 15 - May 21 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Gilles Simon | Win | 6-1, 6-4 |
| Second Round | Alex Molcan | Loss | 2-6, 6-7 (4-7) |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Giulio Zeppieri | Win | 6-3, 6-4 |
| Second Round | Pablo Carreno Busta | Win | 6-4, 2-6, 6-1 |
| Third Round | Stefanos Tsitsipas | Loss | 6-4, 0-6, 3-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Lucas Pouille | Loss | 3-6, 4-6 |
| Serbia Open | ||
| Surface: Red Clay | Date: Apr. 18 - Apr. 24 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Roman Safiullin | Win | Retired |
| Quarterfinals | Thiago Monteiro | Win | 7-5, 6-4 |
| Semifinals | Novak Djokovic | Loss | 6-4, 1-6, 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Diego Schwartzman | Loss | 7-6 (7-5), 3-6, 3-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: 23 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Tommy Paul | Loss | 4-6, 6-3, 6-7 (3-7) |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: 25 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jenson Brooksby | Loss | 0-6, 3-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alex De Minaur | Win | 6-3, 6-7 (1-7), 7-5 |
| Second Round | Novak Djokovic | Loss | 3-6, 6-7 (2-7) |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Feb. 14 - Feb. 19 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Mackenzie McDonald | Win | 7-6 (7-3), 6-3 |
| Second Round | Emil Ruusuvuori | Win | 7-6 (7-4), 6-3 |
| Quarterfinals | Marin Cilic | Win | 3-6, 6-3, 6-4 |
| Semifinals | Roberto Bautista Agut | Loss | 6-2, 3-6, 5-7 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexei Popyrin | Win | 6-7 (4-7), 6-1, 7-6 (8-6) |
| Second Round | Cameron Norrie | Loss | 4-6, 6-7 (5-7) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: 28 |
| Round | Opponent | W / L | Result |
| First Round | Denis Kudla | Win | 3-6, 6-3, 6-2, 7-6(7-2) |
| Second Round | Benjamin Bonzi | Win | 6-4, 6-0, 7-5 |
| Third Round | Rafael Nadal | Loss | 3-6, 2-6, 6-3, 1-6 |
| Adelaide International 2 | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Gianluca Mager | Win | 7-5, 6-3 |
| Quarterfinals | Arthur Rinderknech | Loss | 6-7 (7-9), 5-7 |
| Adelaide International 1 | ||
| Surface: Hard | Date: Jan. 3 - Jan. 9 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Steve Johnson | Win | 6-4, 4-6, 6-2 |
| Quarterfinals | Egor Gerasimov | Win | 7-5, 6-3 |
| Semifinals | Marin Cilic | Win | 7-6 (7-3), 6-3 |
| Final | Gael Monfils | Loss | 4-6, 4-6 |
